Imide-linked maleimide and polymaleimide compounds

Abstract

The invention is directed to maleimide thermosets incorporating imide-extended mono-, bis-, or polymaleimide compounds. These imide-extended maleimide compounds are prepared by the condensation of appropriate anhydrides with appropriate diamines to give amine terminated compounds. These compounds are then condensed with excess maleic anhydride to yield imide-extended maleimide compounds.

What is claimed is: 
     
       1. A compound having the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         each of R and Q is independently selected from the group consisting of a substituted or an unsubstituted aliphatic, aromatic, heteroaromatic, siloxane, unsaturated hydrocarbon, polyester, polyamide and polyurethane moieties; 
         X is a polymerizable or a curative moiety; and 
         n is an integer having the value between 1 and about 10. 
       
     
     
       2. The compound of  claim 1 , wherein the polymerizable moiety is selected from the group consisting of a cationic polymerizable moiety, an anionic polymerizable moiety, a ring-opening polymerizable moiety and a free radical polymerizable moiety. 
     
     
       3. The compound of  claim 1 , wherein the curative is selected from the group consisting of phenol, a phenyl ester, an anhydride, a thiol, an amino, a carboxyl, an alcohol moieties and any combination thereof. 
     
     
       4. The compound of  claim 1 , wherein the polymerizable moiety selected from the group consisting of is vinyl ether, vinyl ester, an acrylate, a methacrylate, an epoxy, an oxetane, an oxazoline, a benzoxazine, vinyl chloride, an urethane, norbornyl, maleimide, phenol, a phenyl ester, styrenic, a propargyl ether, a cyanate ester, nadimide and combinations thereof. 
     
     
       5. The polymer of  claim 1 , wherein each of R and Q is independently selected from the group consisting of:
 (a) a substituted or an unsubstituted linear, branched, cyclic aliphatic and alkenyl moieties having between 2 and about 500 carbon atoms; and 
 (b) a substituted or an unsubstituted aromatic or heteroaromatic moieties having between 6 and about 20 carbon atoms. 
 
     
     
       6. The compound of  claim 1 , wherein the compound is an imide-extended bismaleimide having the structure: 
       
         
           
           
               
               
           
         
         wherein: 
         each of R and Q is independently selected from the group consisting of a substituted or an unsubstituted aliphatic, alkenyl, aromatic, heteroaromatic and siloxane moieties; and 
         R 2  is selected from the group consisting of H and methyl, 
         with the further proviso that the imide-extended bismaleimide is not 
       
       
         
           
           
               
               
           
         
       
     
     
       7. The compound of  claim 6 , wherein each of R and Q is independently selected from the group consisting of:
 (a) substituted or unsubstituted linear, branched, cyclic aliphatic and alkenyl moieties having between 2 and about 500 carbon atoms; 
 (b) substituted or unsubstituted aromatic or heteroaromatic moieties having between 6 and about 20 carbon atoms; and 
 (c) substituted or unsubstituted siloxane moieties having between 2 and about 1000 silicon atoms. 
 
     
     
       8. The compound of  claim 7 , wherein each of R and Q is independently selected from the group consisting of substituted or unsubstituted siloxane moieties, wherein the siloxane moieties are polysiloxanes comprising repeating units selected from the group consisting of dimethylsiloxane, methylphenylsiloxane, diphenylsiloxane, methylhydrosiloxane, and combinations thereof. 
     
     
       9. The compound of  claim 7 , wherein the substituted aliphatic, alkenyl, aromatic, heteroaromaticor siloxane moieties comprise substituents selected from the group consisting of an alkyl, an alkenyl, an alkynyl, hydroxy, oxo, an alkoxy, mercapto, a cycloalkyl, a substituted cycloalkyl, a heterocyclic, a substituted heterocyclic, an aryl, a substituted aryl, a heteroaryl, a substituted heteroaryl, an aryloxy, a substituted aryloxy, a halogen, a haloalkyl, cyano, nitro, nitrone, an amino, an amido, —C(O)H, —C(O)—O—, —C(O)—, —S—, —S(O) 2 —, —OC(O)—O—, —NR—C(O)—, —NR—C(O)—NR—, —OC(O)—NR—, wherein R is selected from the group consisting of H, a lower alkyl, an acyl, an oxyacyl, carboxyl, carbamate, sulfonyl, sulfonamide and sulfuryl. 
     
     
       10. An adhesive composition comprising:
 (a) between 0.1 wt % and about 5 wt % of at least one curing initiator based on total weight of the composition, the curing initiator comprising a free-radical initiator or a photoinitiator; and 
 (b) at least one
 imide-extended bismaleimide of  claim 6 .